We’re in Milan to see what goes into a model fitting there. Cindy tries on Dolce & Gabbana’s Spring ’93 collection, and the Italian duo feature more of the long, lean, lithe, Brit-rock-gone-hippie looks that were popular that season. We're talking floppy hats, clogs, chunky heels, peasant blouses, maxi skirts, chokers, patchwork, and massive ’70s collars. There’s even a bit where the girls dress up in matching, shrunken mod suits like the Beatles in the early Brian Epstein years. Linda Evangelista, with her perfectly bobbed hair, plays John Lennon, and is slightly embarrassed by the prospect of fake-playing a guitar.

Cindy talks about the process: finding your rack, going through all the adjustments, having your Polaroid taken for reference so you know how the pieces go together and what accessories go where (this was the year, after all, when everyone wore gobs of necklaces, gold rings, massive cameos, hats, feathers and scarves) and how her assignment—number 11—sets her order in the show. She jokingly remarks that she’s been bumped down from having opened the show last year.

Cindy introduces us to Domenico Dolce and Stefano Gabbana, and then sits down with them as a journalist to discuss their inspiration for the season and their shared appreciation of breasts—their favorite body part on a lady. It’s amusing to note that Carla Bruni is wearing a replica of the Queen’s crown given that she’s since been First Lady of France. But it’s a beret-wearing Madonna, with overly plucked eyebrows and perfectly in-sync circle Lennon glasses, jumping onstage for the encore that steals the show. Asked about her presence, Madge simply replies that she and the designers are friends. The collection is sprawling and stunning, and it’s lovely for us to see a runway show in the time before livestreaming and backstage cams from this many vantage points.

We’re at Fashion Week after hours with Naomi Campbell, Linda Evangelista, and Kristen McMenamy. The three striking women are visibly fatigued after a long day of fittings and shows, and we get a genuine, loopy vibe from them that gives this behind-the-scenes footage a sense of honesty. They’re just too beat to put up veils. Not that Naomi has ever had any problems being herself, but seeing three supermodels sitting on the floor of a hotel bathroom (a very nice hotel bathroom, mind you) holding up chicken cutlet boob inserts and commenting about their lack of “tits” is remarkably engaging.

After Linda goes home, Kristen and Naomi play dress-up. Naomi puts on a dress that cost her $15 with a $10 poncho. Kristen models a number of her characteristically gothy black dresses, and then Naomi shows off her one-of-a-kind purple suedeAnna Sui ensemble. Kristen leaves (only after jumping all over Naomi’s enormous bed), and then Naomi begins her nighttime ablutions. She’s wearing an oversized tie-dyed tee as she washes her face and exfoliates. It’s an intimate, memorable moment not only because she muses about her future husband, but also because, when she’s traded all her pretty togs for a night shirt and no makeup, she looks very much the young girl that she is. Then she does something awesome: Without any self-consciousness about being on national television, she applies zit cream to her face with a Q-Tip: “I’ve got zits so I’m going to put my spots cream on and I don’t care. Everybody has zits.” It’s humanizing and feels impossibly far away from the Naomi we know today, what with the phone-throwing tantrums and diva behavior.

Photographer Mario Testino goes on a rainy day photo shoot in Milan in 1992.Photo: MTV

Street photography is nothing new now, what with the proliferation of work from Scott Schuman (The Sartorialist) and Tommy Ton (Jak & Jil) and every subsequent riff on the theme, but it’s interesting to see how legendary fashion photographer Mario Testino shot scenes from Milan. First of all, we can’t neglect to mention how beautifully dressed the photographer is, in an impeccably layered, unmistakably Italian ensemble: French cuffs, a jolt of color in his cardigan, a tartan umbrella and a navy blazer with an ASCOT. It’s everything you’d see in a GQgallery of the Italian trade show Pitti Uomo today (though I appreciate that Pitti happens in Firenze).

Testino talks about how much he loves shooting architecture in black and white (accompanied by the requisite shots of the Duomo), but he also talks about how much he loves shooting details like messy electrical wiring above a storefront. The end results are unfussy and lovely. Testino describes how much he loves taking photos of children and older people when he’s shooting for pleasure, adding that older generations have all the style. It’s an admirable quirk for an artist renowned for capturing the most beautiful supermodels of the time, but he’s not alone in this sentiment. Check out Ari Seth Cohen’s Advanced Style blog, that features chic women in their 80s and 90s. It's fabulous... As is Mario’s admirably thick head of hair.

Designer Stephen Sprouse returns to fashion with a collection shot for 'Harper's Bazaar' in 1992.Photo: MTV

On hiatus since December 1988, the artist, photographer and designer Stephen Sprouse returned to fashion with “CyberPunk,” a 32-piece capsule collection made exclusively for Bergdorf Goodman. After a shoulder injury forced a switch to shoes with Velcro fastenings and a commission from Axl Rose of Guns N’ Roses to create tour outfits, Sprouse decided to create a line of androgynous clothing that exclusively featured Velcro closures. To commemorate the occasion, the designer shot a fashion editorial for Harper’s Bazaar.

To give you a little background as to the significance of Sprouse’s return to fashion, you must first know that he was an important figure in the downtown New York scene. He made clothes for his neighbor Debbie Harry; he collaborated with Andy Warhol, creating prints with the artist’s camo silkscreens. Sprouse also worked with Keith Haring, who designed his signature “squibbles” for a number of garments in Sprouse’s 1983 collection. However, the younger generation may better remember Sprouse’s Day-Glo graffiti hand style from the 2008 Marc Jacobs Louis Vuitton ads shot by Terry Richardson, where the designer appears naked with a “defaced” LV monogram weekender hiding his privates. The 2008 collection of “It Bags” were actually an homage to the collaboration between Marc and Steven in 2000, before the artist passed away due to heart failure in 2004.

In a Harper’s Bazaar article in 2008, Jacobs said of Sprouse, “He had this desire to take what he saw in the streets and elevate it. He was using all this stuff that was so costly, really beautiful materials, and he was doing it all so beautifully. There are so many people who try to affect a street style, but it doesn't have the integrity. Stephen's work was so stylistic, and it had street cred.”

Sprouse abandoned fashion to focus on his art career, but resumed making clothes for two collections. CyberPunk’s least expensive piece was a pair of men’s undergarments that retailed for $500, but it’s the luxe ponchos, floor-length hooded tunics, military detailing and post-apocalyptic armor plating that are notable for their fit and dramatic flair: streetwear gone wildly couture.

If you’ve never flipped through Kevyn’s books— The Art of Makeup, Making Faces and Face Forward, which show transformations of regular people into historical figures or turn Hollywood stars into… other Hollywood stars—you absolutely should. Before your favorite YouTube makeup artist showed off step-by-step instructions on how to turn herself into Jared Leto or Justin Bieber, there was Kevyn Aucoin (who died of organ failure, caused by an addiction to the prescription painkillers he took for a pituitary tumor), turning Martha Stewart into Veronica Lake and Christina Ricci into Edith Piaf. Kevyn had a featured column in Allure and was one of the most celebrated makeup artists of his day.

In this segment, Kevyn (along with makeup artist Carol Shaw) teaches us how to pluck our eyebrows. Or, rather, how to overpluck them, since this was the early ’90s, when a pencil-thin arch and a lip-lined pout were all the rage. It’s the video version of the magazine illustration that always told you to take a pencil and point it towards your nose and make sure your nostril and the fat part of the brow met at a certain angle. However, the best advice comes from Carol Shaw, who tells us to use a white nail pencil (a device that helped whiten French manicure tips—another beauty casualty of the decade) to mark where you wanted to pluck, and to use a stiff, angled brush and eyeshadow to fill in the brow and finish the look.

For most of us, Cindy Crawford was the most memorable House of Style host, so it’s with a heavy heart that we bid farewell to the supermodel as she turns 30. I only bring up her age because she does, and in this segment from Cindy’s going-away party, she jokes that it’s not that she’s too good for videotape (she was pursuing a film career at the time), but that she’s too old for it. True to Cindy’s low-key style, she tries on a number of dresses that were called in for the occasion, but ends up wearing her own clothes. Her cropped shirt and pants are Gucci and her glam squad chat as she gets ready.

Cindy arrives alone, cracking jokes the whole time, and checks in with designer and HOS regular Anna Sui. Losing a longtime host can be a tumultuous change for a show, and the two talk about the impact House of Style has had on the fashion community. “Well, I think it’s brought fashion into the home,” says Sui. “I think it’s given us the recognition that we probably never would have gained without being on. And I think it’s given us a whole new audience.”

It is the end of the era, in that Cindy Crawford’s ascension to stardom coincided with the first couple of years of House of Style. The big-haired, bodacious, buxom goddess is no longer the desirable aesthetic ideal of the late ’80s and the early ’90s. Shoulder pads have been traded for flannel shirts, the supermodel has been usurped by the waif, musicians and skaters are making fashion and power has shifted from the European runways to the street. It’s sad to see Cindy go, but it’s exciting to see what's next.

Being a host can have a slew of hilarious moments. Watch Cindy’s evolution as a television host in a series of outtakes, from spaz-outs to laughing fits to getting bundled up in massive blankets between takes. Note that, by the end, Cindy 86es some of the more “cheesy” stuff.

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